New resveratrol oligomers in the stem bark of Vatica pauciflora

Ito, Tetsuro; Tanaka, Toŝhiyuki; Iinuma, Munekazu; Iliya, Ibrahim; Nakaya, Ken‐ichi; Ali, Zulfıqar; Takahashi, Yoshikazu; Sawa, Ryûichi; Shirataki, Yoshiaki; Murata, Jin; Darnaedi, Dedy

doi:10.1016/s0040-4020(03)00730-0

Cited by 95 publications

(115 citation statements)

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“…14) As discussed in previous articles, the behavior of some protons in stilbene oligomers is very complicated. 3,4,[22][23][24][25] Therefore, further spectroscopic evidence in connection with steric factors are required for the accurate determination of the configuration in stilbene oligomers such as 1 and related compounds.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

“…30) 2-b-glucopyranosyloxyphenanthrene-4,6-diol (9), 31) paucifloroside A (11), 23) cis-(Ϫ)-eviniferin (12), 32) upunoside D (13), 33) balanocarpol (14), 34) melanoxylin A (15), 35) malibatol (16), 36) (Ϫ)-ampelopsin F (17), 37) pauciflorol B (18), 23) vaticanol C (20), 38) hemsleyanols C (21) and D (22), 39) pauciflorol C (23), 23) vateriaphenol B (24), 4) nepalensinol G (25), 40) stenophyllol A (26), 41) vaticanol B (27), 38) vaticasides B (28) and C (29), 42) and upunaphenol F (30). 43) The other known compounds were identified to be flavonols [kaempferol 3-O-rhamnoside (31), 44) kaempferol 3-O-rhamnopyranosyl-(1→2)-rhamnopyranoside (32), and quercitrin (33) 45) ], diterpenes [columbin (34) 46) and palmarin (35) 47) ], bergenin (36), 11) and syringin (37).…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

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Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleDipterocarpaceaeous plants have been known to have an abundance of stilbene oligomers that have a blocking unit of resveratrol. The woody plant Vateria indica LINN. (Dipterocarpaceae) is distributed in India and Sri Lanka, and the resin has been used as a traditional medicine for sore throat, chronic bronchitis, rheumatism, and diarrhea.1) The stem of the genus Vateria is known to produce biologically active compounds such as oligostilbenoids and monoterpenes. [2][3][4][5][6] Our previous study demonstrated that the leaves also contain stilbene derivatives in high quantity. 6) Recently, the bioactivities of stilbenoids isolated from Dipterocarpaceaeous plants have been reported to have antimicrobial activites, 7,8) antitumor activities, [9][10][11] and regulation of endoplasmic reticulum stress. H COSY, and heteronuclear multiple bond connectivity (HMBC). Stereostructures were proposed by analysis of nuclear Overhauser effect spectroscopy (NOESY), differential rotating frame Overhauser enhancement (ROE), and ROESY spectra, as well as high-resolution (HR) FAB-MS and electrospray ionization (ESI)-MS analysis and circular dichroism (CD) spectroscopic properties. Vateriaphenol F (1) has a unique C 2 -symmetric structure. Results and DiscussionVateriaphenol F (1) and vaterioside A (2) were purified from an acetone extract of V. indica by open column chromatography on DMS, octadecyl silica (ODS), Silica gel, and Sephadex LH-20, as well as HPLC. Vaterioside B (4) was purified from MeOH extract by repeated chromatography.Vateriaphenol F (1) ([a] D 25 Ϫ136°), obtained as a pale-yellow solid, showed positive reaction to Gibbs reagent. The structure is composed of four resveratrol units (A-D; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a). A detailed elucidation was carried out as follows. The molecular formula was assigned to C 56 H 44 O 13 by HR-ESI-MS that showed a pseudomolecular ion [MϩNa] ϩ at m/z 947.2670, indicating 35 degrees of unsaturation. In the 1 H-and 13 C-NMR spectra at rt, some signals due to ring A 2 were broadened in various solvents. In the 1 H-NMR spectrum in acetone-d 6 at Ϫ30°C, the signals due to Pharmacognosy, Gifu Pharmaceutical University; 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan: b Institute of Microbial Chemistry, Tokyo; 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan: and c Survey of Medicinal Plant Unit, Central Council for Research in Ayurveda and Siddha; Tirunelveli-627002, Tamil Nadu, India. Received June 23, 2010; accepted July 15, 2010; published online July 16, 2010 Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C 2 -symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolu...

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Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A monoglycosidic compound 2, paucifloroside A (1a) has been recently isolated from the stem bark of Vatica pauciflora. 12 However, 1a had a different glycosidic linkage point (C-13b) as depicted in Fig. 1.…”

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confidence: 98%

A New Glycoside of Resveratrol Dimer from Stem Bark of Vitis vinifera

Choi¹,

Choi²,

Cha³

et al. 2010

Bulletin of the Korean Chemical Society

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“…Application to formal synthesis of Pauciflorol F. Using the present method, Pauciflorol F 48 , a natural product isolated from stem bark, which has recently been synthesized by Snyder's group 49,50 and Sarpong's group 51 , was synthesized. The starting material 35 was prepared from commercially available 3,5-dimethoxyphenylmagnesium chloride in two steps (67% yield; Fig.…”

Section: Resultsmentioning

confidence: 99%